CN1633458A - Aminomethylene-functional siloxanes - Google Patents
Aminomethylene-functional siloxanes Download PDFInfo
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- CN1633458A CN1633458A CNA03803848XA CN03803848A CN1633458A CN 1633458 A CN1633458 A CN 1633458A CN A03803848X A CNA03803848X A CN A03803848XA CN 03803848 A CN03803848 A CN 03803848A CN 1633458 A CN1633458 A CN 1633458A
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- Prior art keywords
- alkyl
- base
- amino
- sio
- halogen
- Prior art date
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
Abstract
The invention relates to amino-functional organosiloxanes of general formula I [(HO)R2SiO1/2]t[R3SiO1/2]U[R2SiO2/2]p[O1/2SiR12CR22NH2]S (I), in which s represents a whole number, said whole number being at least 1, s + t + u represents the value 2, t or u represent the value 0 or 1, and p represents the value 0 or a whole number from 1 to 100,000, and R, R1, and R2 have the meanings indicated in claim 1, and a method for the production thereof.
Description
Technical field
The present invention relates to the aminomethylene functional silicone and utilize organoalkoxysilane to make the method for these aminomethylene functional silicones.
Background technology
The aminoalkyl group polysiloxane can be used in many application scenarios, comprises the preparation of polyimide and polyetherimide.But because manufacture method is relatively costly, these compounds still can not be relatively on a large scale as commercial use.
For example, described in U.S. Pat-A-5512650, octamethylcyclotetrasiloxane is open with the base catalysis balance of two aminopropyl tetramethyl disiloxanes.The shortcoming of this reaction is: used reactant is expensive two aminopropyl tetramethyl disiloxanes.In addition, long reaction time, and balanced reaction is sometimes above 10 hours.
The additive method for preparing these polysiloxane comprises with organic functional aminosilane cohydrolysis two functional silanes to make these compounds.But the shortcoming of this method is: because amino the existence arranged, can not implement cohydrolysis with chlorosilane, must use organoalkoxysilane to replace.This means, and at first must implement the esterification of chlorosilane before hydrolytic action, and this esterification can cause the loss of valuable alcohol in subsequent hydrolysis.
DE-A-2500020 has described a kind of method of preparation aminomethylene siloxanes.It comprises makes OH-terminated siloxanes and the reaction of secondary amino group methyl-monosilane and eliminates alcohol.The advantage of this method is: siloxanes and organoalkoxysilane reaction, and uneven this reaction mixture, this reaction mixture will cause the lopps by product and not be desirable therefore.The shortcoming of this method is: because secondary amino group official energy, the silicone oil that so makes can not be in order to make (for example) siloxanes-polyimide copolymer, because the primary amino official can be necessary herein.
Summary of the invention
So the purpose of this invention is to provide amino-functional silicone, except that other purposes, these amino-functional silicones can be in order to preparation polysiloxane-polyimide copolymer.
The invention provides the amino-functional organo-siloxane of general formula I:
[(HO)R
2SiO
1/2]
t[R
3SiO
1/2]
u[R
2SiO
2/2]
p[O
1/2SiR
1 2CR
2 2NH
2]
s
(I)
Wherein,
R is the C of hydrogen atom or unit price Si-C bond
1-C
20Alkyl or C
1-C
15-oxyl, wherein each base optional by-CN ,-NCO ,-NR
x 2,-COOH ,-COOR
x,-halogen ,-acryl ,-epoxy group(ing) ,-SH ,-OH or-CONR
x 2Replace, and in each base one or more non-adjacent MU (methylene unit) can by-O-,-CO-,-COO-,-OCO-or-OCOO-,-S-or-NR
x-Ji substitutes, and in each base one or more non-adjacent methynes unit can by-N=,-N=N-or-the P=base substitutes,
R
1Be the C of hydrogen atom or unit price Si-C bond
1-C
20Alkyl, this base optional by-CN ,-NCO ,-NR
x 2,-COOH ,-COOR
x,-halogen ,-acryl ,-epoxy group(ing) ,-SH ,-OH or-CONR
x 2Replace, and wherein each base one or more non-adjacent MU (methylene unit) can by-O-,-CO-,-COO-,-OCO-or-OCOO-,-S-or-NR
x-Ji substitutes, and in each base one or more non-adjacent methynes unit can by-N=,-N=N-or-the P=base substitutes,
R
xBe hydrogen or C
1-C
10Alkyl, this base is optional to be replaced by-CN or halogen,
R
2Be hydrogen or C
1-C
20Alkyl, this base is optional to be replaced by-CN or halogen,
S is at least 1 integer,
The value of s+t+u is 2,
The value of each is 0 or 1 among t and the u, and
P is 0 or 1 to 100000 integer.
The amino-functional organo-siloxane of general formula I has uncle's ammonia functional group, and it is via the siloxanes Atom Bonding of carbon atom and siloxane chain.The reactivity of these uncle's ammonia functional groups is very strong.For example, therefore polysiloxane-polyimide copolymer can easily make with amino-functional silicone.
R can be that aliphatic type is saturated or undersaturated, aromatics, straight chain type or branched chain type.R is preferably the C that non-branched chain type is substituted
1-C
3Alkane its.More preferably R is a methyl.
C
1-C
20Alkyl and C
1-C
20-oxyl R
1Can be that aliphatic type is saturated or undersaturated, aromatics, straight chain type or branched chain type.R
1Preferably have 1 to 12 atom, especially 1 to 6 atom preferably only has a carbon atom or an alkoxyl group Sauerstoffatom and otherwise carbon atom is only arranged.R
1Be preferably straight chain type or branched chain type C
1-C
6Alkyl.Special preferable methyl, ethyl, phenyl, vinyl and trifluoro propyl.
R
2Base can be that aliphatic type is saturated or undersaturated, aromatics independently of one another, straight chain type or branched chain type.R
2Be preferably C
1-C
3Alkyl or hydrogen.R
2Hydrogen more preferably.
The amino-functional organo-siloxane of general formula I preferably has the end capped polydimethylsiloxane of aminoalkyl group of aminoalkyl at least 90% end of the chain.Especially the end capped polydimethylsiloxane of aminoalkyl group that has aminoalkyl group at least 99% end of the chain.
The value of t is preferably 0.
The value of p is preferably 4 to 500.
The present invention similarly provides a kind of method of amino-functional organo-siloxane in order to the preparation general formula I, the wherein organo-siloxane of general formula I I:
[(HO)R
2SiO
1/2]
v[R
3SiO
1/2]
u[R
2SiO
2/2]
q[H] (II)
Organoalkoxysilane reaction with general formula III:
(R
3O)R
1 2SiCR
2 2NH
2 (III)
Wherein
R
3Be optional C by cyano group or halogen replacement
1-C
15Alkyl,
Q is at least 0 integer,
The value of v is 0 or 1,
The value of u is 0 or 1,
V+u=1 reaches
R, R
1And R
2Definition each with above identical.
R
3Similarly can be that aliphatic type is saturated or undersaturated, aromatics, straight chain type or branched chain type.R
3C preferably
1-C
3Alkyl.R
3Be more preferably ethyl or methyl.R
3It most preferably is methyl.
Described in patent SU395371, the organoalkoxysilane of used general formula III for example can reach high productivity by chlorine alkyl (alkoxyl group) dialkyl silane of amination correspondence and make under the pressure in the ammonia environment simply.
The organoalkoxysilane that so makes can reach very apace the hydroxyl-functional silane reaction with general formula I I simply.Can save the use special catalyst in the case.
Implement easily for the reaction between the organoalkoxysilane of the organo-siloxane that makes general formula I I and general formula III, the organo-siloxane of general formula I I must contain hydroxyl.During carrying out, this reaction eliminates pure R
3OH.
In the method for the amino-functional organo-siloxane for preparing general formula I, the alkoxyl silicone alkanes usage quantity of general formula III is decided on treating functionalized silanol radix amount.But,, must add the organoalkoxysilane of equimolar amount at least if attempt to reach the complete functionalization of OH base.
When the water reaction of the silicane of general formula (III) and equivalent at least, the gained hydrolysate is the sily oxide of general formula (IV):
[O
1/2SiR
1 2CR
2 2NH
2]
2 (IV)
R wherein
1And R
2Definition same as described above.
The preferred temperature of implementing this method is 0 ℃ to 100 ℃, more preferably minimum 10 ℃ to minimum 40 ℃.This method can comprise under the situation of using solvent or not using solvent and implementing in the appropriate reaction device.Operation is chosen wantonly at decompression, high pressure or normal atmosphere (0.1MPa) and is implemented down.Subsequently can be under decompression, room temperature or high temperature the pure reaction mixture of institute's formation be removed.
When using solvent, preferred inertia (especially non-proton property) solvent, for example: aliphatic hydrocrbon, as: heptane or decane, and aromatic hydrocarbons, as: toluene or dimethylbenzene.Can use ether equally, as tetrahydrofuran (THF), diethyl ether or MTBE.The usage quantity of solvent is answered full and uniformization of sufficient to guarantee reaction mixture.The boiling point of preferred solvent or solvent mixture or boiling range under 0.1MPa pressure up to 120 ℃.
When the quantity not sufficient of the general formula III organoalkoxysilane that adds general formula I I organo-siloxane, the Si-OH base of residue unreacted can be deposited in the amino-functional organo-siloxane of general formula I or can react with other compound (these compounds and Si-OH radical reaction), so that can reach Si-OH content further reduce and (for example) can be delivered to the end group of unreacted in the silicone oil mixture, this polysiloxane oil mixt can limit and wait the molecular weight reached in the co-polymerization subsequently.It is also unnecessary that intermediate product is separated.
All symbols in the above-mentioned chemical formula are defined independently of one another.
Embodiment
Unless otherwise indicated, in following all embodiment, all quantity and percentage all are benchmark with weight, and all pressure all are that 0.10MPa (definitely) and all temperature all are 20 ℃.
Comparative example 1
In one 1 liters of steel autoclaves, under 100 ℃ of temperature, (Starfire Systems, Troy USA) restrain liquefied ammonia at the autoclave internal reaction with 300 to make 100 gram chloromethyl dimethyl methyl TMOSs.After 5 hours, this mixture is cooled to room temperature, under atmospheric pressure makes the autoclave decompression and add 500 milliliters of dry heptane.The ammonium chloride that will precipitate filters away, by distillment heptane is removed, and by distillment with this product purifying in addition.Make 56 gram amino methyl dimethyl methyl TMOSs at last.
Embodiment 1
At room temperature making 1000 grams, molecular-weight average is 3000 gram/moles, two hydroxy-end capped polydimethylsiloxane and 79.2 gram (1-amino methyl) dimethyl methyl TMOS reactions.By
1H-NMR reaches
29Si-NMR shows: after 30 minutes, all OH bases have been converted into the amino methyl unit and have made two end capped polydimethylsiloxanes of amino methyl.Under reduced pressure by-product carbinol is removed and makes two (amino methyl) polydimethylsiloxanes of 1050 grams.
Embodiment 2:
At room temperature making 1000 grams, molecular-weight average is 3000 gram/moles, two hydroxy-end capped polydimethylsiloxane and 83.2 gram (1-amino methyl) dimethyl methyl TMOS reactions.By
1H-NMR reaches
29Si-NMR shows: after 30 minutes, all OH bases have been converted into the amino methyl unit.By adding the number ml water silane reaction of residue is also under reduced pressure removed made two (amino methyl) tetramethyl disiloxanes.So also by-product carbinol is distilled away.
Embodiment 3
Making 100 grams, molecular-weight average under 50 ℃ of temperature is 13000 gram/moles, two hydroxy-end capped polydimethylsiloxane and 1.85 gram amino methyl dimethyl methyl TMOS reactions.By
1H-NMR reaches
29Si-NMR shows: after 1 hour, all OH bases have been converted into the amino methyl unit.
Embodiment 4
Making 100 grams, molecular-weight average under 50 ℃ of temperature is 28000 gram/moles, two hydroxy-end capped polydimethylsiloxane and 0.85 gram amino methyl dimethyl methyl TMOS reaction.By
1H-NMR reaches
29Si-NMR shows: after 2 hours, all OH bases have been converted into the amino methyl unit.
Embodiment 5
Making 100 grams, molecular-weight average under 100 ℃ of temperature is 1000 gram/moles, two hydroxy-end capped polydimethylsiloxane and 23.8 gram amino methyl dimethyl methyl TMOS reactions.By
1H-NMR reaches
29Si-NMR shows: after 1 hour, all OH bases have been converted into the amino methyl unit.
Embodiment 6
At room temperature make 1000 grams, vinyl: the ratio of methyl be 1: 4, molecular-weight average is that 2500 gram/moles, two hydroxy-end capped poly-methyl ethylene copolymerization dimethyl siloxane and 95.4 restrain amino methyl dimethyl methyl TMOSs and react.By
1H-NMR reaches
29Si-NMR shows: after 0.5 hour, all OH bases have been converted into the amino methyl unit and can detected residual ammonia ylmethyl dimethyl methyl TMOS.
Embodiment 7
At room temperature make 100 grams, trifluoro propyl: the ratio of methyl be 1: 1, molecular-weight average is that 900 gram/moles, two hydroxy-end capped poly-methyl trifluoro propyl siloxanes and 26.6 restrain amino methyl dimethyl methyl TMOSs and react.By
1H-NMR reaches
29Si-NMR shows: after 2 hours, all OH bases have been converted into the amino methyl unit and can detected residual ammonia ylmethyl dimethyl methyl TMOS.
Embodiment 8
At room temperature making 1000 grams, molecular-weight average is 3000 gram/moles, two hydroxy-end capped polydimethylsiloxane and 87.2 gram (1-amino methyl) dimethylethoxysilane reactions.By
1H-NMR reaches
29Si-NMR shows: after 0.5 hour, all OH bases have been converted into the amino methyl unit and have made two end capped polydimethylsiloxanes of amino methyl.Under reduced pressure by-product carbinol is removed and makes two (amino methyl) polydimethylsiloxanes of 1050 grams.
Embodiment 9
At room temperature making 1000 grams, molecular-weight average is 3000 gram/moles, two hydroxy-end capped polydimethylsiloxane and 71.2 gram (1-amino methyl) dimethyl methyl TMOS reactions.By
1H-NMR reaches
29Si-NMR shows: after 30 minutes, 90% OH base has been converted into the amino methyl unit and has made the end capped polydimethylsiloxane of amino methyl.Under reduced pressure by-product carbinol is removed and makes the amino methyl functional polydimethylsiloxanes of 1050 grams.
Embodiment 10
At room temperature making 215 grams, molecular-weight average is 860 gram/moles, two hydroxy-end capped polydimethylsiloxane and 59.8 gram (1-amino methyl) dimethyl methyl TMOS reactions.By
1H-NMR reaches
29Si-NMR shows: after 30 minutes, all OH bases have been converted into the amino methyl unit and have made two end capped polydimethylsiloxanes of amino methyl.Under reduced pressure by-product carbinol is removed and makes two (amino methyl) polydimethylsiloxanes of 1050 grams.
Embodiment 11
119 gram (1-amino methyl) dimethyl methyl TMOSs are dissolved in 200 ml methanol and with 10 gram distilled water reactions.Stir and afterwards solvent methanol was removed and this product is distilled in 30 minutes.Make two (amino methyl) tetramethyl disiloxanes of 93 grams (productive rate is 97%) at last.
Embodiment 12
At room temperature making 180 grams, molecular-weight average is 1800 gram/moles, the end capped polydimethylsiloxane of monohydroxy (implementing the anionic polymerization effect by the C3 lopps makes) and 12.0 gram (1-amino methyl) dimethyl methyl TMOS reactions.By
1H-NMR reaches
29Si-NMR shows: after 30 minutes, all OH bases have been converted into the amino methyl unit and have made the polydimethylsiloxane of mono amino methyl blocking.Under reduced pressure by-product carbinol is removed and makes 190 gram amino methyl polydimethylsiloxanes.
Claims (8)
1. the amino-functional organo-siloxane of general formula I:
[(HO) R
2SiO
1/2]
t[R
3SiO
1/2]
u[R
2SiO
2/2]
p[O
1/2SiR
1 2CR
2 2NH
2]
s(I) in the formula,
R is the unit price C of hydrogen atom or Si-C bond
1-C
20Alkyl or C
1-C
15-oxyl, wherein each base optional by-CN ,-NCO ,-NR
x 2,-COOH ,-COOR
x,-halogen ,-acryl ,-epoxy group(ing) ,-SH ,-OH or-CONR
x 2Replace, and in each base one or more non-adjacent MU (methylene unit) can by-O-,-CO-,-COO-,-OCO-or-OCOO-,-S-or-NR
x-Ji substitutes, and in each base one or more non-adjacent methynes unit can by-N=,-N=N-or-the P=base substitutes,
R
1Be the unit price C of hydrogen atom or Si-C bond
1-C
20Alkyl, this alkyl optional by-CN ,-NCO ,-NR
x 2,-COOH ,-COOR
x,-halogen ,-acryl ,-epoxy group(ing) ,-SH ,-OH or-CONR
x 2Replace, and in each alkyl one or more non-adjacent MU (methylene unit) can by-O-,-CO-,-COO-,-OCO-or-OCOO-,-S-or-NR
x-Ji substitutes, and in each alkyl one or more non-adjacent methynes unit can by-N=,-N=N-or-the P=base replaces,
R
xBe hydrogen or the optional C that replaces by-CN or halogen
1-C
10Alkyl,
R
2Be hydrogen or the optional C that replaces by-CN or halogen
1-C
20Alkyl,
S is at least 1 integer,
The value of s+t+u is 2,
The value of each is 0 or 1 among t and the u, and
P is 0 or 1 to 100000 integer.
2. amino-functional organo-siloxane as claimed in claim 1, wherein R is straight chain type C
1-C
3Alkyl.
3. as the amino-functional organo-siloxane of claim 1 or 2, R wherein
1Be selected from methyl, ethyl, phenyl, vinyl and trifluoro propyl.
4. as the amino-functional organo-siloxane of one of claim 1-3, R wherein
2Be selected from C
1-C
3Alkyl and hydrogen.
5. as the amino-functional organo-siloxane of one of claim 1-4, it has aminoalkyl group at least 90% chain terminal.
6. the method for preparing the amino-functional organo-siloxane of following general formula I:
[(HOR
2SiO
1/2)
t[R
3SiO
1/2]
u[R
2SiO
2/2]
p[O
1/2SiR
1 2CR
2 2NH
2]
s (I)
Wherein, the organo-siloxane of following general formula I I:
[(HO)R
2SiO
1/2]
v[R
3SiO
1/2]
u[R
2SiO
2/2]
q[H] (II)
Organoalkoxysilane reaction with following general formula III:
(R
3O)R
1 2SiCR
2 2NH
2 (III)
In the formula,
R is the unit price C of hydrogen atom or Si-C bond
1-C
20Alkyl or C
1-C
15-oxyl, wherein each base optional by-CN ,-NCO ,-NR
x 2,-COOH ,-COOR
x,-halogen ,-acryl ,-epoxy group(ing) ,-SH ,-OH or-CONR
x 2Replace, and in each base one or more non-adjacent MU (methylene unit) can by-O-,-CO-,-COO-,-OCO-or-OCOO-,-S-or-NR
x-Ji substitutes, and in each base one or more non-adjacent methynes unit can by-N=,-N=N-or-the P=base substitutes,
R
1Be the unit price C of hydrogen atom or Si-C bond
1-C
20Alkyl, this alkyl optional by-CN ,-NCO ,-NR
x 2,-COOH ,-COOR
x,-halogen ,-acryl ,-epoxy group(ing) ,-SH ,-OH or-CONR
x 2Replace, and in each alkyl one or more non-adjacent MU (methylene unit) can by-O-,-CO-,-COO-,-OCO-or-OCOO-,-S-or-NR
x-Ji substitutes, and in each base one or more non-adjacent methynes unit can by-N=,-N=N-or-the P=base replaces,
R
xBe hydrogen or the optional C that replaces by-CN or halogen
1-C
10Alkyl,
R
2Be hydrogen or the optional C that replaces by-CN or halogen
1-C
20Alkyl,
R
3Be the optional C that replaces by cyano group or halogen
1-C
15Alkyl,
Q is at least 0 integer,
The value of v is 0 or 1,
The value of u is 0 or 1,
V+u=1 reaches
The value of p is 0 or 1 to 100,000 integer.
7. method as claimed in claim 6, wherein R
3Be C
1-C
3Alkyl.
8. make the method for the silane of general formula (III) and water reaction with the siloxanes that generates general formula (IV):
[O
1/2SiR
1 2CR
2 2NH
2]
2 (IV)
In the formula, R
1And R
2Each such as claim 6 qualification.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10206124.6 | 2002-02-14 | ||
| DE10206124A DE10206124A1 (en) | 2002-02-14 | 2002-02-14 | Aminomethylene functional siloxanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1633458A true CN1633458A (en) | 2005-06-29 |
Family
ID=27674631
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA03803848XA Pending CN1633458A (en) | 2002-02-14 | 2003-01-23 | Aminomethylene-functional siloxanes |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20050085612A1 (en) |
| EP (1) | EP1474465A1 (en) |
| JP (1) | JP2005517749A (en) |
| CN (1) | CN1633458A (en) |
| DE (1) | DE10206124A1 (en) |
| WO (1) | WO2003068845A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107001638A (en) * | 2015-04-27 | 2017-08-01 | 瓦克化学股份公司 | Method for producing the organo-silicon compound with amino |
| CN107075256A (en) * | 2014-11-07 | 2017-08-18 | 瓦克化学股份公司 | Crosslinkable organopolysiloxane compositions |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10303693A1 (en) * | 2003-01-30 | 2004-08-12 | Consortium für elektrochemische Industrie GmbH | Aminomethylene functional siloxanes |
| DE10358060A1 (en) * | 2003-12-11 | 2005-07-14 | Wacker-Chemie Gmbh | Process for the preparation of highly viscous organopolysiloxanes |
| DE102004014217A1 (en) * | 2004-03-23 | 2005-10-13 | Wacker-Chemie Gmbh | Crosslinkable compositions based on organosilicon compounds |
| DE102007037198A1 (en) * | 2007-08-07 | 2009-02-12 | Wacker Chemie Ag | Crosslinkable compositions based on organosilicon compounds |
| US7781554B2 (en) * | 2008-03-05 | 2010-08-24 | Bausch & Lomb Incorporated | Polysiloxanes and polysiloxane prepolymers with vinyl or epoxy functionality |
| DE102010001071A1 (en) * | 2010-01-21 | 2011-07-28 | Robert Bosch GmbH, 70469 | Tetraaminodisiloxanes and polyamides prepared therewith |
| DE102016201633A1 (en) * | 2016-02-03 | 2017-08-03 | Wacker Chemie Ag | Process for the preparation of amino-containing organopolysiloxanes |
| JP7310894B2 (en) | 2019-08-09 | 2023-07-19 | 信越化学工業株式会社 | Method for producing primary aminosiloxane compound |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE902190C (en) * | 1950-06-30 | 1954-01-21 | Dow Corning | Process for the preparation of new aminomethylsiloxanes |
| US2942019A (en) * | 1956-10-12 | 1960-06-21 | Union Carbide Corp | Organosilicon methylideneamino compounds and process for producing the same |
| DE1196869B (en) * | 1960-05-14 | 1965-07-15 | Bayer Ag | Process for the preparation of polymethylsiloxanes bearing aminomethyl groups |
| US3544498A (en) * | 1968-07-17 | 1970-12-01 | Gen Electric | Detergent resistant silicone polish |
| BE756928A (en) * | 1969-10-01 | 1971-03-16 | Bayer Ag | POLYSILOXANES AMINOMETHYL-SUBSTITUTES AS WATER-REPELLENT COATINGS AND GLOSSY |
| DE2500020A1 (en) * | 1975-01-02 | 1976-07-15 | Bayer Ag | Alpha-aminomethyl-polysiloxane prepn. - from silanol end-stopped polysiloxanes and aminomethyl-monoalkoxysilanes with immediate alcohol removal |
| US4496705A (en) * | 1984-01-04 | 1985-01-29 | General Electric Company | Synthesis of zwitterionic siloxane polymers |
| US5512650A (en) * | 1986-06-20 | 1996-04-30 | Minnesota Mining And Manufacturing Company | Block copolymer, method of making the same, diamine precursors of the same, method of making such diamines and end products comprising the block copolymer |
| GB9311509D0 (en) * | 1993-06-03 | 1993-07-21 | Dow Corning | Process for the preparation of organopolysiloxanes |
-
2002
- 2002-02-14 DE DE10206124A patent/DE10206124A1/en not_active Withdrawn
-
2003
- 2003-01-23 JP JP2003567967A patent/JP2005517749A/en not_active Withdrawn
- 2003-01-23 WO PCT/EP2003/000701 patent/WO2003068845A1/en not_active Application Discontinuation
- 2003-01-23 CN CNA03803848XA patent/CN1633458A/en active Pending
- 2003-01-23 EP EP03739443A patent/EP1474465A1/en not_active Withdrawn
- 2003-01-23 US US10/504,351 patent/US20050085612A1/en not_active Abandoned
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107075256A (en) * | 2014-11-07 | 2017-08-18 | 瓦克化学股份公司 | Crosslinkable organopolysiloxane compositions |
| CN107001638A (en) * | 2015-04-27 | 2017-08-01 | 瓦克化学股份公司 | Method for producing the organo-silicon compound with amino |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003068845A1 (en) | 2003-08-21 |
| EP1474465A1 (en) | 2004-11-10 |
| US20050085612A1 (en) | 2005-04-21 |
| DE10206124A1 (en) | 2003-09-04 |
| JP2005517749A (en) | 2005-06-16 |
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